Category: Tools – Productivity

A: It’s a kind of advanced calendar which has the power to schedule itself.

Slowly but surely, these AI-powered calendar apps are making their way into the lives of early adopters. They are looking for a way to boost the number of tasks they can manage effectively.

Taking over the grunt work of managing a calendar full of tasks, these apps do more than blindly shuffle around tasks and appointments. Instead, they act as intelligent agents, responding to the actions users take each day. This interplay, they report, is quite game-like: it can be immersive, challenging and fun at the same time. In this article, I describe the ways people play with their auto-schedulers and the impact this will have on the future of personal productivity.

Although the idea has been around for decades, recent advances in cloud computing and Artificial Intelligence (AI) have made auto-scheduling a practical reality. I started using one about 18 months ago and cannot imagine ever going back: it’s become a part of my new, daily routine.

In the first two articles in this series (here and here) on the gamification of task management, I described a number of games which users of task management apps are trying to play. I outlined six levels of technique/app usage which users climb up, as shown in the diagram below.

They don’t make this journey for idle reasons. Those who climb quickly are the ones who are trying to manage increasing numbers of time demands. In other words, in an effort to eke out greater personal capacity, they travel from Levels 1 to 6.

Furthermore, as I pointed out at the start of this series, this is more than a grim endeavor. They are hoping to achieve a game-like, engaging experience as they make their journey. Unfortunately, they haven’t found much luck. Few designers at any level have paid serious attention to the user experience or made any efforts to seriously transform it. At most, they make cosmetic differences.

As a result, while every functioning adult on the planet manages their tasks at one of these six levels, only a few million use electronic task apps. Do the math: out of three billion people with access to the internet, the biggest task management app only accounts for 10–20 million regular users.

That represents a huge gap. Plus an opportunity.

At Level 6, where the technology is new, the idea of auto-scheduling isn’t widespread. The most recent feature at this level is one offered by Todoist Smart Scheduling. It’s their first foray into Level 6 features, but they aren’t the first.

SkedPal, the developers of which I have done work for, is the most mature product and the one I currently use. Timeful, which was acquired by Google, Sheldonize, TimeTo and Focuster round out the collection of known players in the niche.

A comparison of apps at this level versus those found at Levels 3 and 4 show a big difference. They function as static databases, repositories of tasks. If the user adds in due dates or start-dates for tasks, the program reports which ones are overdue at any point in time, but that’s all.

Level 6 applications promise an experience that’s quite different. They are responsive — like the difference between using a monitor that offers touchscreen capabilities versus one that doesn’t.

In these programs, when you make a change to your tasks or calendar, they reply with a fresh new schedule. Multiple changes can be introduced one at a time, or grouped altogether. Sometimes the results it produces are surprising.

SkedPal users I interact with are regularly delighted (or shocked) by the calendar the program creates, the task which it suggests you work on next. Without the tool, you simply would not have remembered.

This makes sense. These programs are meant to do much more than your mind can do, in just a split-second. Now, there’s no danger in creating as many tasks as you like. As you enter hundreds of new ones or change a whole bunch at a time, the program responds the same way: with a fresh,optimized schedule.

This interactive give-and-take makes the UX game-like. You change your inputs and receive a different reaction each time. With continued use, as I show below, you become more productive in response to its unique feedback.

It’s obviously not a tool everyone would appreciate or use. Many have no need for its power. But there are hard-working people who find these capabilities useful, according to my research and experience.

Who Level 6 Users Are

Most users who migrate to these apps generally do so after making an effort to master Levels 4 and 5.

At Level 4, they used a Complex To-do list program that helped them store and view their tasks in different ways. At Level 5, they have substituted these apps with a digital calendar, which they use to juggle their tasks manually.

As I mentioned in the two prior articles, these two techniques have their limitations. While they are perfect for users who have fewer time demands, they both fail to meet the needs of users who manage a large number of tasks. Once they pass a particular threshold, Level 4 and 5 approaches get in the way.

A few get unstuck by using Level 6 auto-schedulers. To understand why they make the switch, let’s analyze their behavior using the same approach used in my prior two articles in the series: The Job to Be Done framework, and the mechanics of gamification.

The Job Level 6 Users Are Trying to Get Done

If you are a Level 6 user, you hire the technologies and techniques offered by auto-schedulers to accomplish three specific purposes.

Reason #1 — You are looking for a way to manipulate a large number of tasks, and want the app’s robotic features to save you time. With it, you should be able to create a schedule and refresh it in seconds rather than hours. You are no longer a victim of an unplanned interruption or the passage of several days.

Reason #2 — You hope to expand the feeling of being on top of things. Perhaps it has been lost for some time and now you want it to be restored. Or maybe it’s become fleeting and you want it to be continuous.

Reason #3 — You expect to experience an increased sense of mastery, a growth in your capacity. You want to be able to do more and therefore achieve new goals. You hire Level 6 apps in order to become a measurably more productive person who never allows tasks to fall through the cracks.

These are sound reasons. Each of them indicates the kind of expectation a Level 4 or 5 user would have if they were up-leveling, having decided to hire a Level 6 app.

However, my 18-month experience points to a far greater possibility. Beyond the three reasons, there are other reasons to hire an auto-scheduler.

New users of auto-schedulers quickly learn that the app needs to be run almost every workday, preferably early in the morning. The logic is simple: the schedule for yesterday is now stale. Anything that was left incomplete must be rescheduled by the app.

Also, things change from day to day, as you complete tasks and generate new ones as a result. Some become obsolete. The project you thought was important is deprecated, forcing you to change gears.

Auto-schedulers can do more than respond to these changes — one day they will capture unique data and build a database which reflects your behavior. When this happens, it will provide you with two further reasons to deepen your use of an auto-scheduler.

Further Reason #1 —Most people become “Total Task Schedulers” when they adopt Level 5 behaviors: they begin to manage the majority of their tasks in their calendar. Now, at Level 6 they can use the app’s data to improve this skill. While it’s possible to gather your own data at Level 5, a good auto-scheduler should provide you some unique insights into your performance in this area. For the first time, you can examine historical data, looking for strengths and weaknesses.

For example, if you are failing to visit the app every workday, the system’s data should reflect your inability to develop this habit, and perhaps suggest the creation of a mitigation plan.

Further Reason #2 — Not only can you focus on improving your skills, you can also use the data to improve the quality of your schedules. Each day when you reschedule your calendar, a good auto-scheduler should indicate the likely success of your schedule. For example, a calendar that is too tightly packed should throw up a red flag.

These two reasons don’t represent trivial attempts. Instead, they present an opportunity for app designers to educate and engage users, converting them from “users of an app” into “players of a game” whose expectations change over time.

In today’s world, that’s a given in well-designed video-games. Once a player moves past the entry level, they provide abundant opportunities to make measured improvements. Most of these new levels can’t be perceived at the start: they only become revealed with higher accomplishment.

The only difference here is that the game being played is “real.” In other words, it comes from a real-life situation, rather than the heavy fiction/fantasy used to construct a game like Angry Birds. Although the initial context is different, the fact is that all games are based on a common pool of mechanics as I mentioned in the prior articles. Fictional or non-fictional: they can both be made to be engaging.

While SkedPal does not have these levels built in, my experience has evolved, just as it would in a video-game. Here are some of the games I have found myself playing, even though the app doesn’t recognize them.

The Games Level 6 Users Try to Play

As I mentioned, all well-designed video-games consist of distinct levels which require higher levels of skill. Here are three “phases” I have discovered which can be used to craft these levels.

Games at the Learning / Onboarding Phase

As I mentioned, new users spend the bulk of their time, in the beginning, trying to understand how an auto-scheduler works. For example, SkedPal makes a clear distinction between fixed and flexible tasks, keeping the former unchanged, while optimizing the placement of the latter. This distinction is new to most users.

Also, the user is asked to provide a set of weekly time maps. These user-defined graphs map out preferred zones such as “early weekday mornings between 6am and 9am” or “book reading times between 6pm and 8pm on weekends.”

One of the first games to master in this phase is one I alluded to before: a “Daily Practice Game.” It’s simply the habit of entering the app on a daily basis in order to optimize one’s calendar. Mastering this practice is a small but essential win-state, similar to the one achieved by players of Farmville. They learn early in the game that there is a penalty for ignoring for several days: it results in the death of their crops.

Another game users could play is related to one of the first things they want to know when they log in — “Which tasks have become stale?” As I mentioned before, they need to take action to bring everything current. This daily action could be part of a “Task Recovery Game” which takes a certain amount of time and activity which could, in the future, be measured.

Occasionally, these changes are not sufficient and the player must also adjust a part of their task infrastructure, such as a time map. This could be part of a Framework Adjustment Game” in which the customizable components of the app are used to refine one’s schedule.

These three games are all built on the recurrent actions needed to keep an auto-scheduler running smoothly. As of today, I don’t know of any app which overtly promotes these games, but as I mentioned before, the potential exists to weave them into the onboarding experience.

My limited research shows that in the absence of explicit support, each of these games is played quite poorly at first. Over time, things improve as users teach themselves the required underlying behaviors. However, if they were offered as part of games at an introductory level, there might be more who make it to the next phase.

Some do make the transition and after a while, the behaviors become habits. When that happens they up-level to the next phase.

2. Games at the Features Phase

In the next phase, the user learns to exploit the program’s more sophisticated features. For example, version 2.0 of SkedPal indicates when there is a problem with your newly updated schedule.

It offers a Hot List which reflects the number of tasks which cannot be scheduled due to logical problems. For example, if you scheduled a task with a hard due-date for yesterday but didn’t complete it, the task would not be rescheduled. Instead, it would show up on the Hot List as an issue to be addressed.

A player could adopt a “Hot List Game” in which the user tries to minimize the total number of errors produced. SkedPal also indicates when a task is scheduled too tightly by adding a highlight to it in the form of a small icon. Avoiding these highlights could be part of a “Too-Tight Game.”

Another game is related to a feature I mentioned before: the way SkedPal distinguishes between your fixed and flexible tasks. The program synchronizes your fixed calendar in Outlook/Google with your internal calendar of flexible tasks. Unknown to some, it also allows the creation of additional fixed calendars.

I happen to use two fixed calendars. One acts as an appointment calendar with other people. The other is set up for personal appointments (with myself) and also to insert buffer times. Appointments with myself are solo tasks which occur at fixed times, such as workouts at the gym. Buffer time-slots are used to make sure I don’t over-schedule myself: each day, I have 1–2 hours of unscheduled time.

They are both used to ensure I maintain a balanced calendar which isn’t unrealistic. It’s a “Calendar Balance Game.”

Games at this phase and the one below it represent an important start, but I think they only scratch the surface. As I play them, I have generated lots of questions related to my usage.

3. Questions at the Self-Knowledge Phase

While games at this phase don’t actually exist, I continually ask myself questions which indicate that they are likely to be played in the future. Here are some of the questions I have about the schedule I produce each day:

– Is my current schedule too tight and therefore unrealistic? What is a lead metric of its quality?

– Are there items which are being postponed several times? Which ones are they?

– Are my time estimates unbiased?

– How often does a suggested next task actually get done? Why? Why not?

– What is the likelihood of a scheduled meeting actually taking place as scheduled?

There are also questions I have related to my skills as a “Total Task Scheduler.” I’d like to know:

– What is my track record for following my schedule and doing what I planned to do?

– What practices should I change to improve my skills?

– Are my high priority tasks being completed before those of lower priority?

– How often do I abandon my schedule to do something entirely different?

– Are there trends in my scheduling I need to be aware of?

– How many tasks in my system are actually dead and should be deleted?

I see each of these questions as the seeds of future games. They require their own metrics which could be collected by auto-schedulers. Put together here in their raw form they represent a start. I’m interested to hear from you in the Comments, especially if you have other questions that we should be asking at this phase.

What Designers Can Do

In the world of video-game design, there is an important role defined as a “Level Designer.” This person’s job is to create the missions, locales and stages of each level in a particular game. They possess a distinct skillset which is critical: they keep players engaged long after the Onboarding Stage, turning a player’s curiosity into a near-obsession.

Their skills could be applied to the phases I have shared above, to carve out levels of self-knowledge which I believe players of task management crave. As you may imagine, this job requires equal doses of psychology and computer science.

Unfortunately, I only know one or two developers who are thinking along these lines. Most are so close to their product and its functionality that it’s hard to step away to ask and answer these broader questions. They take time, plus no small measure of introspection.

But this is to be expected, according to Clay Christensen and other innovation experts. There’s an in-depth interplay between users and apps that must be studied over time. Answers and insights, they warn, don’t come from surveys or focus groups.

Instead, designers and developers must stand far out in the future, ahead of their users. Way out. It’s the only way to divine their needs, the jobs they are trying to get done and the games they want to be engaged by.

It’s a worthwhile effort.

Why should the most engaging software available to use be limited to trivial pursuits such as shooting angry birds or taking pictures of virtual characters?

Why can’t we put more effort into developing apps which help us learn skills which are important? Why can’t users become immersed in activities that help them get better, even as they complete important tasks? Wouldn’t we all be better human beings if we helped each other bring the fun of game-play to the stuff we really care about?

If there’s an epic quest someplace for task management app designers, and even game developers, perhaps it lies in answers to these questions.

Recently, I write an article on Medium geared towards designers of task management “apps” ranging from those who support the use of memory, to paper, to task management apps, to calendars to auto-schedulers. In the article, I shared the following graphic that shows the progression that users make as they

progress from the use of one skill level to the next. As you may recall, the idea that different tools are needed for different task volumes is a key research finding here at 2Time Labs.

In this article, I use two different tools to analyze this progress, explaining that a transformation actually takes place (or is struggling to emerge.) It happens when the user is able to experience their task management as a game.

Unfortunately, their game-play is thwarted by several factors. One is that they are unaware of this journey and a second is that many task management software designers are also blind to the whole picture.

This means that people aren’t engaged. Their apps are dull, even though the contents are vital to their everyday lives.

An Amazing Time Demand Tracker… It doesn’t exist… so don’t go looking for it… but if it did, it would be a gadget used to track individual commitments.

Backing up a bit… A time demand is defined by 2Time Labs as an individual commitment to complete an action in the future. It’s a discrete, mental creation that disappears once the action is complete and is usually made up of a provisional action, duration and likely start time.

The problem is that time demands are hard to track. People who capture with high skill immediately record them in a safe place, such as a paper pad, smartphone or program like Evernote. From there, the time demand is acted upon in one of several ways once it’s emptied from the point of collection. It’s tossed away, acted on immediately, stored, scheduled or added to a list.

The challenge is that no-one (to my knowledge) has ever tried to track time demands. No tool exists to answer even basic questions such as:

– how many are created per day on average

– how long they sit in a capture point before being emptied

– how many end up being disposed in each of the different ways I listed above

The right kind of device would need a human interface due to the fact that time demands enter our lives in different ways, some of which are mental in nature e.g. during a dream.

There ARE studies, for example, of email flow, but this is too imprecise – some emails are filled with time demands while others require only one – “delete it immediately without even reading.” Too many time demands are simply made up in response to an arbitrary, unrecorded stimulus.

If this device existed, it would open up the doors to all kinds of research, and experimentation that could change the way we think of time management. Perhaps there is someone willing to invest?

In earlier posts, I stepped into the future and imagined what it would be like to have a calendar that sat inside your watch, and projected a calendar in front of you in the form of a virtual touch-screen that you could manipulate at will.

Well, here’s a calendar tool for the iPad that makes it a much easier task than I have ever seen. It’s not a projector that sits in a wrist-watch, but moving around the segments in a schedule in this manner seems to be just as easy as I had imagined.

Most of us think of schedules in linear terms, the way we think of calendars and diaries. Along comes the Muji Chronotebook to change all that, with the first circular daily schedule I have ever seen.

It’s based on the face of a clock, and the 12 hours that it represents. Each activity looks like a slice of a pie, and it seems deceptively easy to plan a full day using a layout that looks like the analog clocks that most of us older folk grew up with.

It’s whimsical, traditional and nostalgic, and the fact that there is no software or app that uses this concept, means that it’s all about pen/pencil and paper.

As I dug through academic papers on the topic of time management over the past few days, I came across a journal article that was simply amazing in its prescience. It was written by Steve Whittaker and Candace Sidner of Lotus Development Corp (now part of IBM.) It was published in 1996, and they also happen to be the authors who coined the term “email overload.”

ABSTRACT
Email is one of the most successful computer applications yet
devised. Our empirical data show however, that although email was originally designed as a communications application, it is now being used for additional functions, that it was not designed for, such as task management and personal archiving . We call this email overload. We demonstrate that email overload creates problems for personal information management: users often have cluttered inboxes containing hundreds of messages, including outstanding tasks, partially read documents and conversational threads. Furthermore, user attempts to rationalise their inboxes by filing are often unsuccessful, with the consequence that important messages get overlooked, or “lost” in archives. We explain how email overloading arises and propose technical solutions to the problem.

What is amazing to me is not the point they are making, as it’s one that’s been echoed here at 2Time many times, especially in my posts suggesting ways to improve Outlook. Instead, what’s startling is that no-one seems to have paid any attention.

Not only have Outlook and other email management programmes failed to offer anything new, Gmail didn’t even exist at the time this article was written, and it committed the same design mistake by not recognizing that existing email management software isn’t fashioned around its most common use — task and time management.

I received an interesting email from a reader of 2Time site who felt a bit put off at my comments about paper systems.

She mentioned that in my video on “Permanently Fixing the Weekly Review” I said (in passing) that paper systems are from the 1950’s. Well, of course, all paper systems are from the pre-1990s, because that’s just about all we had back then to work with!

But I have never addressed the main point she’s inquiring into — can a paper-based system be every bit as good as one that’s electronic? Her last question was the most pointed:

If we truly believe in the “know the basics and make it your own” philosophy, then we must allow people to use the tools that speak to who they are. There cannot be a wrong way.

I humbly agree! In fact, I do all my manual capturing on paper. I also use a Palm PDA – they sit beside each other in a portable wallet that I carry everywhere.

However, using the 11 Habits as a tool for analyzing a time management system that uses only paper reveals that there is a limit to the number of time demands that can be handled using only paper. Let’s look at each of the fundamentals and see why a paper system prevents a user from reaching the higher belts in some disciplines, and why.

(As you read this, bear in mind that the 2Time belt system is just something I made up… it’s not written in stone anyplace. If you’d like to see a short summary of each of the fundamentals, simply do a search on this blog for the relevant keywords in bold and you’ll find my very first definitions.)

Capturing: At the moment I prefer to use paper because it has the following characteristics…

it’s cheap

requires no charging

it can get wet or hot

it’s quick to use – I can write faster than I can type, or have my handwriting recognized

On the other hand, it also offers no backup capabilities, which actually helps me because it leads me to Empty more frequently.

When it comes to automatic capture points, however, those that are electronic win hands-down. For example, at some point soon, letters and bills will be replaced by email entirely.

In the future, I fully expect that tools like LiveScribe will become easier to use, and that we’ll have paper and electronic combinations that give us some of the benefits of both media.

In 2Time terms, it’s possible to become a Green Belt in Capturing using either paper or electronic tools.

Emptying: I think it’s equally easy to empty a paper capture point as it is to empty an electronic capture point. However, there is something that feels good about crossing an item off my pad that deleting doesn’t quite match.

Apart from that, most professionals’ time demands arrive via email and having a paper capture point alongside an electronic email Inbox is a little cumbersome as one needs to move between two different media.

But these are minor differences. The act of Emptying can be mastered if only paper tools are used, so there is little difference between the two.

Tossing: There are only some minor differences between Tossing using paper or electronic tools. Green Belts are achievable regardless of the medium.

Acting Now: Once again, there are very minor differences between the two media in this particular fundamental.

Storing: The discipline/fundamental of storing is defined as indexing information that’s needed in the future so that it’s easy to find at the precise moment of need. This is one fundamental that paper proves to be a limiting factor.

Important information that most professionals need in the future include:

In 2Time terms, it’s not possible to progress to the Green Belt stage without using electronic tools. To put it another way, someone who uses electronic tools can effectively executive this fundamental for a greater number of items.

For example, trying to store passwords is a problem for anyone who has a great number of them, and tries to manage them using paper only. Once they upgrade to an electronic storage system with automatic backups, and master the new habits needed, they become more effective.

Scheduling: This fundamental is one that clearly separates paper from electronic users in terms of the number of scheduled items they are able to manage.

A quick glance at the detailed posts on Scheduling reveals that it’s not possible to manage a complex, dynamic schedule on paper. Again, this is strictly a matter of volume.

Users that want to manage a great number of time demands have greater success using a complete and dynamic schedule, alongside short lists. This isn’t a problem at White and Yellow belts, where the number of time demands is low. However, as the number increases, and it becomes harder to handle a mental schedule, then the techniques at Orange and Green Belt levels become necessary.

A dynamic schedule, by the way, is one that can be changed on the fly, when needed. The power of portable electronic PDA’s and smartphones is that a schedule can be carried and accessed quickly. Laptops aren’t quite as accessible, of course.

An electronic schedule can also be duplicated and synchronized in real time across multiple platforms, which makes it easy to recover from a catastrophic event.

Listing: The problems with paper-based Scheduling are similar to those of paper-based Listing. With electronic lists come the safety of having good backups, easy updates from any geographic location plus platform synchronization.

At the White and Yellow Belt levels, where Listing is a prominent activity, using paper lists is risky because of the lack of backups.

Interrupting, Switching, Warning and Reviewing: These Advanced fundamentals are tool independent — they don’t have much to do with using paper or something electronic.

As I performed the above analysis for the first time for this article, I realized that I should reinforce some of the important ideas behind Time Management 2.0, to explain why I created a system that requires electronic tools at the higher Belts.

No-one needs to be at any particular Belt in time management. My only recommendation is professionals should choose the Belt that fits their “style,” and allows them to manage their chosen volume of daily time demands.

White Belts are not inferior or superior to Green Belts, any more than a huge pipe is better than a small pipe. They are simply designed for different purposes. At the same time, choosing the wrong pipe cam lead to chaos. When it comes to a particular skill in any fundamentals, it’s important that the selection be made carefully, and in keeping with key metrics like “the number of emails I receive each day.”

There is a common belief that a time management system should be tool-neutral. I think that a modern system includes one’s “choice” of:

habits

gadgets

software

Each person assembles a system that matches their life needs, and as such, the choice of gadget (which might range from a Franklin Planner to an Android) is very important. I certainly am dealing with this issue as I plan my next upgrade to a Blackberry, as it will make some habits harder to execute, and others easier, simply because of its design.

Bottom Line: as we upgrade and tinker with our time management systems we are free to use what we will, but there are “hard” consequences to our choices that we must account for, and simply can’t ignore.

P.S. Let me know your thoughts in the comments below. The great thing about writing a blog is that I’m not stuck with what I created even last week!

When you work directly with an Outlook Calendar, the Reminder function becomes quite useful as a tool for Interrupting. You can set the reminder to go off a the moment a task is supposed to start, or for some time period before it’s due to commence.

However, Outlook only gives you a few methods of disposing of a Reminder. It pops up in a list, and you can ignore the pop-up altogether and continue what you were doing. To dispose of it, however, you need to eithera) click on Dismiss, which removes the reminder and leaves the item in your calendar, never to return to your awareness
b) delay the reminder for a few minutes
c) open the reminder and reschedule the task for a later time

What it doesn’t do that it should is allow you to mark the item as “completed.”

There should be an extra box that allows this option, much in the same way that it does in the Smart Diary Suite. If the item could be marked as completed, it could then be crossed out in Outlook, showing that it was successfully done.

This would be a benefit in a few ways:

1. there’s a psychological boost that we get by crossing out items that are complete. It simply feels good, and looking over a calendar of completed items that are crossed out would also feel good, as you can see in the diagram above

2. it would provide a record of what actually got completed, which would help people like me who keep track of their time each week. If it also kept a record of when the item was marked as complete, that would be even better.

When the philosophy is not clear, then the features follow suit. These programs have some nice doo-dahs, but they aren’t built around the fundamentals of time management, so they don’t fit the time management needs of many professionals. Check out my series on articles on Outlook’s shortcomings, or do a search on the keyword Outlook for more.

Meta

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